The recommended approach is to add a view with this checkbox in that particular region of your shell window using either View Discovery or View Injection. For more information on these two topic, you could take a look at the following sections on MSDN:

I do not know your exact scenario, but if you consider necessary to reference your shell windows from a view, I would suggest you to share more details of your scenario that help to clarify this situation. This way, we could find a possible approach that
fits with your scenario.